Why Your Debt Payoff Timeline Might Be the Thing That Is Making You Quit

Money Files

If you have debt and a dream, you have probably told yourself at some point that you have to choose between the two. That you have to be debt-free before you buy the house, before you start a family, before you invest in your future. And on the surface that feels like the responsible thing to believe. But what I have watched happen with so many of the people I work with is that waiting for the debt to be gone before the dream can start is the very thing that guarantees neither one ever moves.

In this episode I want to name two specific stalls that show up when debt feels like it is standing between you and what you want, because I do not think most people are having this conversation with themselves out loud. The first stall is avoidance, and it is sneakier than you think. It does not always look like ignoring your bank account. Sometimes it looks like telling yourself that if you just earned more the debt would not be a problem, or giving yourself permission to keep spending because the balance is already high and nothing is moving fast enough to feel worth it anyway. The second stall is fear of the timeline and the scale, where the size of the dream or the size of the debt feels so overwhelming that you quietly take the whole thing off the table without ever saying out loud that you gave up.

I bought a house before I paid off my student loans. I never gave up on that dream even when the numbers told me I could not afford it yet. What I did instead was stay curious, play with the numbers, and keep asking what decisions I needed to make to get there. That orientation is what this episode is really about, because there is a difference between believing in your dream while you are still doing the work and using your dream as a cover for quitting on yourself, and most people do not realize which one they are actually doing.

In this episode you’ll learn…

[00:05:10] What the avoidance stall actually looks like when you are trying to pay off debt, including the subtle ways it shows up as a YOLO mentality, a focus on future earnings, and losing interest in the plan because progress is not happening fast enough

[00:10:30] Why your timeline expectation for paying off debt might be the thing driving your avoidant behaviors, and what it actually means to commit to becoming debt-free without being attached to how quickly it happens

[00:15:45] Why the $800 payment that brings a $30,000 balance down to $29,720 matters more than the number suggests, and the question to ask yourself about who you became in the 30 days it took to make that payment

[00:20:20] How the fear of scale and timeline stall shows up when your dream feels too big or your debt feels too high to even bother starting, and why not allowing yourself to get curious about the goal guarantees the outcome you are most afraid of

[00:25:40] The difference between believing in your dream while you are still living your life and using your dream as a cover for quitting on yourself, and how to honestly tell which one you are actually doing right now

[00:29:15] The one question to ask yourself every single month to find out whether you are still taking ownership of your debt payoff and your dreams or whether you have quietly stopped trying without realizing it


Tune in to this episode of Money Files to understand the two stalls that keep you stuck when debt and dreams feel like they are competing so you can stop waiting to be debt-free and start building the life you actually want at the same time.



Are you ready to start asking for help with your finances? Apply to work with me, and let’s start working towards your financial goals.



If you loved this episode on pursuing your dreams while paying off debt and finally breaking the cycle of avoidance, check out Episode 48 How to Use Financial Dreams to Pay Off Debt and Save Money.


Transcript for “Why Your Debt Payoff Timeline Might Be the Thing That Is Making You Quit

Intro: Hi, and welcome to Money Files. I’m Keina Newell from Wealth Over Now. I work everyday with professional women and solopreneurs to help them get out of financial overwhelm and shame so they can experience more flexibility and ease with their finances. Are you ready to gain confidence and learn to manage your finances intentionally? Tune in and grab financial tips that will help you master the way you think about and manage your finances. 

Keina: Hello, and welcome back to another episode of Money Files. I hope today’s podcast lands with you. I’ve been thinking about my own journey of paying off debt, specifically paying off student loan debt. I had over $70,000 worth of debt. I’ve had credit card debt. I’ve even taken on credit card debt as a business owner and had to pay it off. I’ve probably increased my threshold, if you will, with debt, being a business owner because there have been investments that I’ve made to the tune of $25,000. And I have said like yes to the investment, even before I’ve had the money and committed to a plan of paying it off.

So I would say I’ve taken some calculated risk, if you will, and having goals of buying a home. I’ve been exploring new goals in my life and thinking about, in the next 10 years, what do I want life to look like for me financially? Like, where am I living? How much money am I making? And I don’t have certain, not with certainty do I know those answers to some of those questions, but I have just been playing with the ability to dream and have money goals. I think that is something that I have done in the past and then lost sight of it because sometimes I can be very practical. My brain knows that one plus two equals three, but I definitely have examples in my life where I have not been living within the linear nature of how sometimes I feel like in my head numbers work. 

What I want to talk to you about today is more so feelings that you might have around your own debt. So I’ve helped clients that have $2,000 worth of credit card debt. They have $5,000 worth of credit card debt, $80,000 or even $100,000 worth of credit card debt. And one of the things that I would say all of these clients have in common is that they feel like their debt is standing in between their life that they have right now and the life that they actually want. And you might be in a similar position. You’re like, okay, I have debt, but I want to buy a house or I have debt and me and my partner, we’re looking to have a baby or I have debt, but I would also like to be contributing to my retirement. And every time you think about dreaming of what you want in life, and maybe it’s an experience, a certain lifestyle, but every time you think about what you want, the thing that comes up for you is your debt.

And it gets in the way of you being able to dream. So if that’s you, I just want you to know that you’re not alone. You are a very ordinary person. I would say that is a very regular experience that people have. But I want to name something for you is that I don’t want you to get trapped in this belief that if you have debt, you can’t proceed with your dreams. And I’m not saying proceeding with your dreams in a way that may be like, just pretend like you don’t have any debt and I’m going to make decisions and not check the numbers. I’m not saying that. I’m saying more so feeling like you’re trapped by your debt, that you have to choose that you either have to be debt free or you can’t buy the house or you have to be debt free before you actually have the baby or you have to be debt free and then you can invest in your future.

And for you, responsibility feels or looks like that you pay the debt off and then you get access to your dream. But the challenge can be that if your debt is something that makes you feel really overwhelmed, it just feels like something that you’re like, I don’t know where to start. I’m not sure how to tackle this. If it has that type of hold on your life, then what ends up happening is that you don’t make any movement and your movement looks like you avoiding the debt or it looks like I’m not okay with the timeline and what I think it will take for me to pay off the debt. So then I’m also not making any advances. 

I would caution you that I don’t think that you are having this conversation with yourself out loud. You would actually have to sit down and ask yourself, like what are my feelings towards my debt and paying off my debt, when I look at the number, when I think about how many times it’s come back? And you might find that you have this cycle of avoidance or this cycle of it’s going to take forever. So just don’t even worry about it. It’s just going to kind of be me and my debt together forever and always. And I don’t want that for you because what it means is that in five years from now, in 2031, I’m recording this podcast in 2026, in five years from now, you are going to have made limited progress and your salary may have increased. There may be different things in your life that have changed.

You may have gotten married, etcetera, but in five years from now you could potentially see no progress because of the fact that you’re just frozen and you’re so overwhelmed. I don’t want that for you. I want you to be someone who can say like, I can address my debt and I can accomplish my dreams at the same time. One of the first stalls that comes up when you feel really overwhelmed by the amount of debt that you have, especially when it’s standing in the way of like the dream that you have for yourself, I would say the first stall that comes up is avoidance. And that avoidance can look like not actually wanting to check your numbers. If you don’t actually look at your bank account, if you don’t open the credit card statements, then you don’t actually have to know and face the numbers. 

So if you don’t know, you don’t have to feel scared inside. You don’t have to feel ashamed. Like ignorance is bliss for you. The avoidance can also sound like, if I just earned more than my debt wouldn’t it be a problem. It’s a type of situational shame where you’re like, well, if I was in a different situation, then this debt wouldn’t be here. And you go to solve for the problem of paying off your debt by thinking about you somewhere in the future. If I had more money, if I had the raise, if I had the promotion, it could even be passed. Like maybe if I had taken that other job and I would have been able to pay off this debt. So you’re not actually taking ownership of what you could actually be doing right now to change your debt, to get your debt to decrease. 

And sometimes the avoidance can also look like you having a YOLO mentality. So I only live once and I’m just going to give myself permission to spend. I actually don’t think this is as like out loud as I am making it sound, but it goes into a place in a space where you just give yourself permission to add to the debt because you just feel like, well, I mean, it’s already this high anyways. I’m just going to add a little bit more to it. What does it even matter? So you don’t really change anything about your lifestyle. You are still going to concerts. You are still buying plane tickets to go see your friends. You’re still giving family members money. Like you’re doing things every single month that jeopardize you actually being able to pay down your debt. And this isn’t to say that you can’t live your life and pay down debt at the same time, but you’re doing it in a way that’s avoidant, where you’re like, this is just my situation.

So because this is my situation, I’m just going to live in this way because until something changes, then I’m not changing. I’ve seen this with one of my clients right now and it’s a very subtle type of avoidance. But she is someone who I would say sometimes wants to avoid her debt because she feels like things should happen really quickly. And she has evidence in her life of things happening quickly. She’s been very successful and her success has happened quickly. However, she has some debt. She wants to pay down the debt and it’s not happening quick enough. And because it’s not happening quickly, she’s losing interest in being committed to the plan. It doesn’t feel like it’s something that she’s ever going to be able to accomplish. Like she feels like she’s doing everything right, but it’s not happening really quickly.

And when I say this, that she’s doing everything right, she’s not getting in all of the nooks and crannies of whether or not she’s doing everything right. I think if there’s 10 steps to paying down your debt, well, she might be doing eight of them. And she needs to do all 10. And because she’s not doing all 10, it’s not working. So she feels really, really frustrated right now. And the debt is not moving as quickly as she wants it to move. So what’s happening is she’s allowing some more of her, like she’s giving herself permission to spend in ways that if she wasn’t spending money on her family or if she wasn’t spending money on different flight choices, that she could be more intentional about putting money towards her debt.

And I’m saying this because when you are in an avoidant pattern of paying off your debt and it looks like if I just earn more or I’m not going to check my numbers, you are moving yourself further away from your goal of actually paying down debt. And that is your behaviors are the things that are actually shaping how fast you can actually pay down debt. And there’s a disconnect in between your behaviors and the results that you want. I would also, as I’m talking this out right now, I want you to define fast, at the same time, because I think sometimes we define fast as, when we look at your life, it’s like, well, you’ve had a relationship with debt for like 20 years and you want to pay your debt off in six months. 

And we are changing a relationship that you’ve had for 20 years and you may not be able to change that in six months. Like your timeline is a little off and you get frustrated because it’s not fast and you start to have these avoidant behaviors. So you build this story that I can only trust the process if it happens really fast. And when the process feels slow to you, which I would also define like, let’s define slow, you are going to stop trying. So you’re impatient with the process and I think that when you were paying off debt, I think the hardest part is actually getting started and telling yourself like, you know what, I’m committed to paying off my debt.

I’m not committed to the timeline. I’m committed to paying off the debt. I’m committed to becoming the person who has a debt-free lifestyle. Like that’s the person that I’m becoming through this process. It doesn’t mean you don’t mess up. It doesn’t mean, that you don’t use your credit card sometimes, but it is you accepting a new identity as you walk through the process of actually paying off your debt. And I think that the thing that came up for me as I was thinking through this podcast is that when you are paying off your debt, the change from one month to the next, as you see your balance go down, it might feel incredibly insignificant.

If you have $30,000 worth of debt and you make an $800 payment towards that debt, and the next month it’s like $29,720, it might feel very insignificant. But I want to offer who is the person that made that $800 payment? What did she do the last 30 days when she was becoming the person who is debt-free? How did she think? What choices did she make? How did she maintain integrity when it came to the goal of being able to pay off debt? And I say that because every single month that you show up as that new version of yourself, one day you’re going to look up and your debt is going to be paid off. It’ll just be gone. I feel like that’s what happened with my student loans.

Like I didn’t do anything really crazy. Unfortunately, I don’t have a story that’s like I paid off $100,000 worth of debt in six months. I don’t have that story, but I do have a story of being persistent. I have a story of being diligent, setting a plan, following the plan, increasing the plan when I could. Can I add more money? Okay, let me add more money for the next year. Can I add more money this next year? Okay, let me add more money for the next year. My consistency was the thing that helped me pay down debt. But as I was paying off five-figure student loan debt, I also didn’t stop living my life. Like I bought a house before I even paid off the student loan debt. So that’s why I think the identity portion of this is so important to think about who and what is the version of me that pays down that debt. 

So kind of a little off script, but I just wanted to offer that to you because sometimes you’re so stuck on that timeline and what it has to look like in terms of it being fast instead of thinking about who are you becoming along that journey. And then I would say the second thing that shows up as you are trying to be debt free and also reach your dreams is that the second stall, it can show up as fear of like the timeline and the scale of something. So it could show up as like, I have debt and I want to buy a house, but homes are too expensive. So I’m not even worried about buying a house. You’re like, whoa, whoa, whoa, whoa. You just took buying a house off the table.

But why? Like, okay, maybe home prices are more expensive, but you’re going to give up on an entire dream because the scale of it is too big for you. Or you might say like I have $100,000 in debt and there’s no point of even really getting started in paying off my debt. Maybe kids are too expensive, so why even start planning to have a kid? I think when it comes to debt and dreams, some people don’t allow themselves to dream because the scale of the dream just seems too big. The timeline of the dream just seems too big. But what’s actually happening when you think in this way is that you are putting a limitation on your own ability to move forward because you’re scared of the size of the number or you’re scared of how long it’s going to take. And when you do that, then you actually guarantee the outcome that you are afraid of. 

So what happens is that you stay exactly where you are, not because the goal was actually impossible, but because you didn’t allow yourself to actually start playing with the goal and being curious about the goal. So you never created space for your dream. Part of my story is that before I was 30, I bought a house while I was in student loan debt. When I first moved to D.C., I was making like $50,000 and I wanted to buy a home. I went and looked at homes. Turns out your girl couldn’t afford a home making $50,000 in D.C. And I lived in D.C. in my same apartment for five years before I was actually able to buy a home. But here’s the thing. I never gave up on my dream of buying a home. I knew working out the numbers, I was like, oh, I have to make a little bit more before I actually buy a house. But I never gave up on the dream. 

I built like a dream budget to figure out which direction did I want to go and how did I want to navigate? I played with like home numbers all the time. Like, okay, if I need to buy a house that’s $400,000, what would that look like? What would the mortgage look like? Like I played with the numbers to help build a vision for myself. I didn’t give up because of the scale. I didn’t give up because of the timeline. And I would say the same is true. Like I’m giving you an example of buying a home. But I would say the same is true in terms of like being able to pay off debt. If that’s a dream for you because you’re like, okay, if I can pay off this hundred thousand dollars worth of debt, I have money coming back into my cash flow. 

We can’t get caught with the timeline. We can’t get caught with the scale of what we think our dream requires. Instead, we got to lean in and we got to think about, okay, if my goal is to pay off my debt, if my goal is to buy a home, if my goal is to have a baby, we got to get curious about what do I need to do in between now and when this goal comes to life. And I at the time when I wanted to buy a house, I didn’t know that it was going to take me five years to buy a home. But I knew that I wanted to buy a home. So that made me have certain conversations at work about how much money I was earning. It made me think about which jobs would I want to accept versus which jobs was I not going to accept.

So I had a different orientation in how I was thinking about things. Even when I was thinking about paying off my student loans, I wasn’t discouraged if I couldn’t pay them off in five years. Like I didn’t give myself, I should say, a really short timeline because I think that would have stressed me out. It would have discouraged me. Instead, I was looking for what is the possibility here when it comes to the dreams that I have. So yes, I had debt, but I also had plans for, okay, when I make extra money, how can I use this extra money? How can this impact me? What decisions do I need to make in order to realize my dreams? And I’m saying this to you, it wasn’t all perfect, but I never lost sight of my goal. 

So what I want you to hear is that there’s a difference between believing in your dream while you’re still living your life and using your dream as a cover for quitting on yourself. So if you’re someone who has dreams and you feel like your debt is getting in the way, I want you to know that there’s a difference between you believing in your dream and still living your life and using your dream as a cover for quitting on yourself. Maybe from the outside, they look the same. So maybe you have someone with debt who’s spending money. And one version of that is like, I believe this is possible for me and I’m taking ownership of it. And so that person is checking their numbers. They’re asking for help when they need it. They’re making a plan, even if it’s slow. 

The other version is quietly deciding that it’s not going to work and they might as well enjoy themselves right now. And that person is quitting on themselves. So they’re not actually seeing the progress through that they said that they wanted to make. And the part is that most people don’t actually realize that’s what’s happening. Like you actually got to sit down and kind of be honest with yourself. And I would say that you could probably go in between both of these spaces, especially if you have a large amount of debt that maybe is going to take you longer than a year to pay off. You get discouraged and you might become the person that’s quitting on themselves. Or you might be really motivated and you’re the person that’s like, nope, I live my life like I got some debt. I’m spending some money, but I’m like being very intentional about what this looks like.

So I want you to call yourself out if you hear yourself in this and you’re like, oh, I have been quitting on myself in some type of way. So there’s one question I want you to ask yourself, and that is, am I still taking ownership of paying off my debt and reaching my goals? Or have I stopped trying to pay off my debt and reaching my goals? Because your answer to this is going to impact your future decision making. I gave the scenario and thinking about if you quit on yourself in the next five years, you are, I pray, going to be alive. But in the next five years, I want you to look back and think about like, dang, I didn’t know it was going to take me five years to reach this dream. But I’m so glad I didn’t quit on myself. And I want you to be able to see yourself in five years, add five years to your age. And I want you to be thankful that in 2026, you listened to this podcast and you made a decision to stay connected to your dreams, to stay connected to the thought of being debt free and that you unraveled it, you figured it out. 

And ask yourself this question every single month. Am I still taking ownership or have I stopped trying? So I want you to make a choice about why you were actually stuck when it comes to paying off your debt and realizing your dream. Have you found yourself stalling? Are you in this avoidance trap? Do you have timeline fear? So I hope that something that I said today in this podcast, you’re like, okay, Keina, I feel like you called me out a little bit. But I do want you to reconnect to your goals. I don’t want you to give up. Money management, I was talking on a podcast today about money management being a leadership skill. And there are new skills you’re going to have to learn. There are new hurdles that can come up.

And if you know that money management is a leadership skill and it’s something that you’re always going to be learning, a muscle that you’re always going to be using, it’s going to shift your approach and it’s going to change your mindset. So thank you so much for tuning in and have a great week. Until next time.

Outro: Thank you so much for listening to Money Files. If you’re ready to take the next step to reach your financial goals, head to www.wealthovernow.com/appointment and let’s get started.

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